# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_6iprAdenine _database_code_depnum_ccdc_archive 'CCDC 917227' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C7 H10 N2 O2), C5 H5 N5, 4(O)' _chemical_formula_sum 'C19 H25 N9 O8' _chemical_formula_weight 507.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.8173(19) _cell_length_b 11.0856(19) _cell_length_c 13.235(2) _cell_angle_alpha 89.971(10) _cell_angle_beta 69.525(10) _cell_angle_gamma 63.586(11) _cell_volume 1308.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4419 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 21.12 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.959 _exptl_absorpt_correction_T_max 0.972 _exptl_absorpt_process_details multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14288 _diffrn_reflns_av_R_equivalents 0.1035 _diffrn_reflns_av_sigmaI/netI 0.0706 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 24.94 _reflns_number_total 4584 _reflns_number_gt 2733 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+1.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.013(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4584 _refine_ls_number_parameters 330 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0890 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1892 _refine_ls_wR_factor_gt 0.1749 _refine_ls_goodness_of_fit_ref 0.892 _refine_ls_restrained_S_all 0.892 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7818(4) 0.7787(4) 0.2115(3) 0.0738(11) Uani 1 1 d . . . H1 H 0.8383 0.7534 0.2589 0.089 Uiso 1 1 calc R . . C3 C 0.8744(5) 0.6688(4) 0.1069(4) 0.0955(14) Uani 1 1 d . . . H3A H 0.8314 0.6986 0.0533 0.143 Uiso 1 1 calc R . . H3B H 0.8741 0.5847 0.1237 0.143 Uiso 1 1 calc R . . H3C H 0.9756 0.6544 0.0781 0.143 Uiso 1 1 calc R . . C2 C 0.7628(6) 0.9135(5) 0.1872(4) 0.125(2) Uani 1 1 d . . . H2A H 0.7199 0.9359 0.1330 0.188 Uiso 1 1 calc R . . H2B H 0.8586 0.9114 0.1597 0.188 Uiso 1 1 calc R . . H2C H 0.6974 0.9815 0.2530 0.188 Uiso 1 1 calc R . . O1 O 0.3576(2) 0.6845(2) 0.28699(18) 0.0607(6) Uani 1 1 d . . . O2 O 0.3511(3) 0.9600(3) 0.54296(19) 0.0664(7) Uani 1 1 d . . . C6 C 0.6301(4) 0.7877(3) 0.2759(3) 0.0533(8) Uani 1 1 d . . . N1 N 0.3597(3) 0.8186(2) 0.4137(2) 0.0474(7) Uani 1 1 d . . . H1A H 0.2750 0.8266 0.4575 0.057 Uiso 1 1 calc R . . N51 N 0.5550(3) 0.8669(3) 0.3800(2) 0.0547(7) Uani 1 1 d . . . H9 H 0.5970 0.9062 0.4010 0.066 Uiso 1 1 calc R . . C61 C 0.5666(4) 0.7252(3) 0.2412(3) 0.0535(8) Uani 1 1 d . . . H3 H 0.6152 0.6730 0.1710 0.064 Uiso 1 1 calc R . . C8 C 0.4180(4) 0.8865(3) 0.4515(3) 0.0508(8) Uani 1 1 d . . . C10 C 0.4245(3) 0.7385(3) 0.3118(2) 0.0464(8) Uani 1 1 d . . . N5 N 0.8623(3) 0.9727(3) 0.7172(2) 0.0515(7) Uani 1 1 d . . . H5 H 0.8035 1.0255 0.7801 0.062 Uiso 1 1 calc R . . N4 N 1.0660(3) 0.8695(3) 0.5599(2) 0.0505(7) Uani 1 1 d . . . C13 C 0.9620(3) 0.8259(3) 0.5660(3) 0.0475(8) Uani 1 1 d . . . C12 C 0.8364(3) 0.8882(3) 0.6634(2) 0.0463(7) Uani 1 1 d . . . C11 C 0.9986(4) 0.9579(3) 0.6526(3) 0.0539(8) Uani 1 1 d . . . H11 H 1.0410 1.0062 0.6720 0.065 Uiso 1 1 calc R . . C14 C 0.7310(4) 0.7767(4) 0.6210(3) 0.0635(9) Uani 1 1 d . . . H14 H 0.6519 0.7567 0.6382 0.076 Uiso 1 1 calc R . . N7 N 0.8430(3) 0.7103(3) 0.5247(2) 0.0561(7) Uani 1 1 d . . . N6 N 0.7149(3) 0.8680(3) 0.6970(2) 0.0591(7) Uani 1 1 d . . . C15 C 0.9650(4) 0.7327(3) 0.4937(3) 0.0514(8) Uani 1 1 d . . . N8 N 1.0791(3) 0.6654(3) 0.3966(2) 0.0649(8) Uani 1 1 d . . . H8A H 1.0751 0.6090 0.3547 0.078 Uiso 1 1 calc R . . H8B H 1.1561 0.6786 0.3762 0.078 Uiso 1 1 calc R . . C16 C 0.7566(3) 0.2568(3) 0.2173(2) 0.0491(8) Uani 1 1 d . . . H16 H 0.7347 0.1966 0.2668 0.059 Uiso 1 1 calc R . . C18 C 0.6171(4) 0.3421(4) 0.1935(3) 0.0739(11) Uani 1 1 d . . . H18A H 0.5350 0.3983 0.2605 0.111 Uiso 1 1 calc R . . H18B H 0.5921 0.2822 0.1625 0.111 Uiso 1 1 calc R . . H18C H 0.6367 0.3993 0.1426 0.111 Uiso 1 1 calc R . . C17 C 0.8873(4) 0.1656(4) 0.1118(3) 0.0656(10) Uani 1 1 d . . . H17A H 0.9136 0.2217 0.0624 0.098 Uiso 1 1 calc R . . H17B H 0.8588 0.1111 0.0780 0.098 Uiso 1 1 calc R . . H17C H 0.9719 0.1065 0.1284 0.098 Uiso 1 1 calc R . . C19 C 0.6906(3) 0.5138(3) 0.4386(2) 0.0447(7) Uani 1 1 d . . . C20 C 0.9386(3) 0.4479(3) 0.2994(2) 0.0477(8) Uani 1 1 d . . . O4 O 1.0517(2) 0.4640(2) 0.27090(19) 0.0640(7) Uani 1 1 d . . . O3 O 0.5890(2) 0.5850(2) 0.52687(18) 0.0599(6) Uani 1 1 d . . . C21 C 0.7915(3) 0.3464(3) 0.2754(2) 0.0431(7) Uani 1 1 d . . . N10 N 0.8214(3) 0.5210(2) 0.39778(19) 0.0458(6) Uani 1 1 d . . . H10 H 0.8312 0.5756 0.4367 0.055 Uiso 1 1 calc R . . N50 N 0.6812(3) 0.4242(2) 0.37550(19) 0.0455(6) Uani 1 1 d . . . H23 H 0.6013 0.4153 0.3995 0.055 Uiso 1 1 calc R . . C60 C 0.9189(3) 0.3572(3) 0.2373(2) 0.0491(8) Uani 1 1 d . . . H11A H 0.9944 0.3053 0.1700 0.059 Uiso 1 1 calc R . . O5 O 0.7173(3) 0.1257(3) 0.9287(2) 0.0796(8) Uani 1 1 d . . . O6 O 0.6327(3) 0.4042(3) 0.9144(2) 0.0884(9) Uani 1 1 d . . . O7 O 0.2857(3) 0.3902(3) 0.0701(2) 0.1003(10) Uani 1 1 d . . . O8 O 0.4601(4) 0.1140(3) 0.0742(2) 0.1066(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.080(3) 0.088(3) 0.056(2) 0.001(2) -0.007(2) -0.056(2) C3 0.091(3) 0.097(3) 0.083(3) -0.002(3) -0.002(3) -0.056(3) C2 0.154(5) 0.098(4) 0.098(4) -0.003(3) 0.007(3) -0.082(4) O1 0.0650(15) 0.0743(15) 0.0582(14) -0.0038(12) -0.0193(12) -0.0492(13) O2 0.0667(15) 0.0898(17) 0.0502(15) -0.0138(13) -0.0080(12) -0.0543(14) C6 0.057(2) 0.069(2) 0.0429(19) 0.0022(16) -0.0130(16) -0.0422(18) N1 0.0498(15) 0.0600(15) 0.0429(15) -0.0001(12) -0.0137(12) -0.0381(13) N51 0.0545(16) 0.0738(18) 0.0493(17) -0.0011(14) -0.0134(14) -0.0467(14) C61 0.055(2) 0.066(2) 0.0430(18) -0.0025(15) -0.0126(16) -0.0370(17) C8 0.056(2) 0.0631(19) 0.046(2) 0.0023(16) -0.0179(17) -0.0396(17) C10 0.0541(19) 0.0520(17) 0.0448(19) 0.0046(15) -0.0212(16) -0.0331(16) N5 0.0492(16) 0.0538(15) 0.0462(16) -0.0043(12) -0.0147(13) -0.0231(13) N4 0.0544(16) 0.0590(15) 0.0530(17) 0.0087(14) -0.0232(13) -0.0374(13) C13 0.0506(18) 0.0522(17) 0.0495(19) 0.0065(15) -0.0226(16) -0.0300(15) C12 0.0469(18) 0.0476(17) 0.0442(18) -0.0001(14) -0.0173(15) -0.0226(15) C11 0.061(2) 0.0559(19) 0.052(2) 0.0044(17) -0.0241(18) -0.0325(17) C14 0.058(2) 0.072(2) 0.065(2) -0.0006(19) -0.0184(19) -0.0389(19) N7 0.0545(17) 0.0661(17) 0.0542(18) -0.0048(14) -0.0135(14) -0.0397(14) N6 0.0525(17) 0.0647(17) 0.0561(17) -0.0079(14) -0.0150(14) -0.0293(14) C15 0.0518(19) 0.0597(19) 0.048(2) 0.0045(16) -0.0179(16) -0.0319(16) N8 0.0608(18) 0.085(2) 0.0509(18) -0.0153(15) -0.0057(15) -0.0485(16) C16 0.0561(19) 0.0526(18) 0.0450(18) 0.0000(14) -0.0182(15) -0.0322(16) C18 0.072(2) 0.084(3) 0.067(2) -0.011(2) -0.032(2) -0.033(2) C17 0.072(2) 0.068(2) 0.056(2) -0.0121(17) -0.0187(19) -0.0375(19) C19 0.0455(18) 0.0511(17) 0.0413(18) 0.0018(15) -0.0133(15) -0.0288(15) C20 0.0484(18) 0.0537(18) 0.0475(19) 0.0050(15) -0.0155(16) -0.0318(15) O4 0.0513(13) 0.0794(16) 0.0641(15) -0.0064(12) -0.0072(12) -0.0448(13) O3 0.0540(14) 0.0750(15) 0.0495(14) -0.0148(12) -0.0047(12) -0.0412(12) C21 0.0499(18) 0.0450(16) 0.0371(17) 0.0040(13) -0.0147(14) -0.0266(14) N10 0.0452(14) 0.0559(15) 0.0428(15) -0.0030(12) -0.0121(12) -0.0330(12) N50 0.0473(15) 0.0555(14) 0.0403(15) -0.0021(12) -0.0118(12) -0.0338(12) C60 0.0492(18) 0.0535(18) 0.0414(18) -0.0036(14) -0.0089(15) -0.0284(15) O5 0.0862(19) 0.0798(17) 0.0592(16) -0.0133(13) -0.0177(14) -0.0363(15) O6 0.112(2) 0.0914(19) 0.0689(18) 0.0079(15) -0.0338(17) -0.0550(17) O7 0.087(2) 0.124(2) 0.081(2) -0.0129(18) -0.0079(16) -0.0618(19) O8 0.109(2) 0.128(3) 0.0726(19) -0.0109(18) -0.0027(17) -0.072(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.467(6) . ? C1 C6 1.518(5) . ? C1 C3 1.533(5) . ? O1 C10 1.242(3) . ? O2 C8 1.232(4) . ? C6 C61 1.344(4) . ? C6 N51 1.383(4) . ? N1 C8 1.363(4) . ? N1 C10 1.373(4) . ? N51 C8 1.368(4) . ? C61 C10 1.432(4) . ? N5 C12 1.355(4) . ? N5 C11 1.355(4) . ? N4 C11 1.317(4) . ? N4 C13 1.389(4) . ? C13 C12 1.387(4) . ? C13 C15 1.389(4) . ? C12 N6 1.352(4) . ? C14 N7 1.327(4) . ? C14 N6 1.338(4) . ? N7 C15 1.373(4) . ? C15 N8 1.344(4) . ? C16 C21 1.503(4) . ? C16 C17 1.524(4) . ? C16 C18 1.528(5) . ? C19 O3 1.236(3) . ? C19 N50 1.359(4) . ? C19 N10 1.365(4) . ? C20 O4 1.243(3) . ? C20 N10 1.375(4) . ? C20 C60 1.430(4) . ? C21 C60 1.352(4) . ? C21 N50 1.380(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 110.0(4) . . ? C2 C1 C3 111.3(4) . . ? C6 C1 C3 113.2(3) . . ? C61 C6 N51 119.0(3) . . ? C61 C6 C1 126.1(3) . . ? N51 C6 C1 114.9(3) . . ? C8 N1 C10 125.6(3) . . ? C8 N51 C6 124.1(3) . . ? C6 C61 C10 120.5(3) . . ? O2 C8 N1 122.0(3) . . ? O2 C8 N51 123.2(3) . . ? N1 C8 N51 114.8(3) . . ? O1 C10 N1 119.0(3) . . ? O1 C10 C61 125.0(3) . . ? N1 C10 C61 116.0(3) . . ? C12 N5 C11 106.7(3) . . ? C11 N4 C13 102.4(3) . . ? C12 C13 N4 111.2(3) . . ? C12 C13 C15 117.5(3) . . ? N4 C13 C15 131.3(3) . . ? N6 C12 N5 127.7(3) . . ? N6 C12 C13 127.1(3) . . ? N5 C12 C13 105.2(3) . . ? N4 C11 N5 114.5(3) . . ? N7 C14 N6 129.6(3) . . ? C14 N7 C15 118.9(3) . . ? C14 N6 C12 109.8(3) . . ? N8 C15 N7 119.1(3) . . ? N8 C15 C13 123.7(3) . . ? N7 C15 C13 117.1(3) . . ? C21 C16 C17 113.0(3) . . ? C21 C16 C18 111.1(3) . . ? C17 C16 C18 110.0(3) . . ? O3 C19 N50 123.2(3) . . ? O3 C19 N10 121.5(3) . . ? N50 C19 N10 115.4(3) . . ? O4 C20 N10 119.1(3) . . ? O4 C20 C60 125.0(3) . . ? N10 C20 C60 115.9(3) . . ? C60 C21 N50 118.7(3) . . ? C60 C21 C16 125.7(3) . . ? N50 C21 C16 115.6(3) . . ? C19 N10 C20 125.2(2) . . ? C19 N50 C21 124.2(2) . . ? C21 C60 C20 120.6(3) . . ? _diffrn_measured_fraction_theta_max 1.00 _diffrn_reflns_theta_full 24.94 _diffrn_measured_fraction_theta_full 1.00 _refine_diff_density_max 0.697 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.061